That toddlin' town (Chicago)

During the twelve hour overnight bus ride from Toronto to Chicago I received an email from mum which casually mentioned that my old friend Sophie, who was travelling around the US, might have been in Chicago about then. I sent her a Facebook message and fell asleep.

The bus arrived nice and on time – at 5am. I had not counted on the hour time difference. I was highly apprehensive as to what I was going to do in Chicago at 5am in the freezing cold when nothing was open and sunrise was not for two hours. I lingered a little in the bus terminal before making my way to the hostel, hoping sincerely that they had 24 hour reception.

Miraculously, the smiling man at the front desk said my room was ready for me and I was able to check straight in at 5:40am and go to sleep! When I woke up – at about 2pm – I discovered via Facebook message that Sophie was not only in Chicago, and in the same hostel as me, but in the very same dorm room. Apparently she had been commenting to her German friend about the girl sleeping! (I was wearing a hood and eye mask and thus unrecognisable, as it was very cold in the hostel).

After I got up I went to have ‘breakfast’ – a tasty pad thai and spring roll combo from a Thai / Mexican place nearby on Clark Street. I then made my way downtown on the subway, meaning to join the Hop on Hop off bus tour – but as it was after 4pm by the time I found the spot it began, the driver said there were no more sellers selling tickets that day. No matter: I would do it with Sophie the next day, which suited better anyway.

On the way to the Hop On Hop Off tour stop at Millennium Park, I found State Street (that Frank Sinatra sang about), walked around and photographed Millennium Park – including the giant silver ‘bean’ and fancy big fountain structures with faces on them -, and admired the beautiful buildings of Chicago’s skyline.

Afterwards I walked around the city a little, reading an interesting architectural billboard that explained the origins of some old buildings in the street, before stopping in a cafe to have a coffee.

Back at the hostel I met up with Sophie and her German friend Christina and the three of us went to a nearby Italian restaurant the others had loved. I had some very tasty lobster ravioli. We the headed back to get ready as Sophie and I were heading to the hostel-organised trip to a nearby Blues Bar.

We joined the hostel crew to the blues bar and at 9:30pm enjoyed some high quality blues from a four-piece band. At 10:30pm a band in the other room came on, so we shifted over. This band was not as enjoyable.Sophie left at about 11pm but I lingered to talk to some of the others from the hostel – one Spaniard recognised me from a five minute conversation at the Monday night hostel outing in New York the previous week!

At around 11:30pm I headed towards the hostel. However, I took a wrong turn up Lincoln Avenue and promptly discovered a live music venue called Lincoln Hall, outside and inside which many people were mingling. I went inside and quickly discovered that the live music act had finished and people were filtering home – except for a group of three locals at the bar whose night appeared to be just beginning.

It transpired that it had been one of their 29th birthday (it was now just past midnight) and none had to work the next day so I joined them heading to two more bars, at each of which they knew the bartender. This turned out to be most enjoyable and fortuitous: nobody back at the hostel had had a clue where to head that night without local knowledge.

Unbeknownst to my new friends, the first place we went to after Lincoln Hall was holding an amateur comedy night. Most were terrible except one, and as the birthday boy John was himself an aspiring standup comedian, he entertained us with witty heckling from the sidelines.

When this place closed at 2am we went to a final place that was still kicking on until 4am on a Monday night. Surprisingly they were serving a full menu all night and I had a meal of fried chicken, coleslaw and bread at about 3am. All night my new friends entertained me with exaggerated Chicago accents and a head of corn that somebody had acquired. I’m not really sure what that was about, but the locals took delight in pronouncing it ‘cann’ in their fake Chicago accents, for my benefit.


Back at the hostel the next morning Sophie and I headed off to the Hop on Hop off bus tour. We managed to get straight on it at Millennium Park, skipping one bus that was full up top in favour of a near empty one just behind it. This proved a good choice: our guide was excellent, his commentary effortless and entertaining. We rode the tour the whole way: this took about two hours. By the end we were hungry so headed to the allegedly famous Giordano’s pizza, of which there was a location right near stop 1.

In this restaurant we ordered the deep dish pizza, which claimed to be a Chicago special. A tad crestfallen when the waitress informed us the wait would be 30-40 minutes, we whiled away the time catching up until it eventually came. By the time it did, we were very hungry. And what came was an odd quiche-like structure: the crust was more pie than pizza and the topping was piled high, especially the cheese. Naturally, we ate too much.

We decided to waddle to the Hancock center and go up top to the observatory. This proved both a good idea and perfect timing: the sun was just starting to set and the views were beautiful through the clear glass, as opposed to the wiry mesh of either the CN tower – or as Sophie said, the Seears tower in Chicago, up which she had already been. It was also not at all busy like the Seears tower.

Many photos later, we headed back to the hostel to get ready for that night’s pub outing. We met the same small group of guys from the previous night and had a relaxing chat for about an hour and a half at a nearby Irish pub before both of us decided to call it a night and head back to the hostel.

The next day we set off for downtown again to go straight to Buckingham Fountain, which Sophie said I ought to go to. Afterwards we (eventually) found the nearby Hop on Hop off stop and rode it three more stops to Navy Pier – this guide was not as good as our previous day’s.

At Navy Pier we stopped for lunch at Harry Daley’s – an evidently Chicago-born chain, judging by the Chicago baseball paraphernalia inside and the Chicago references all over the menu. I had probably the most delicious (and way too big) nachos I’ve ever had.

We wandered a little around the pier before heading back to the hostel. Sophie then chose a run to the foreshore: I elected to nap. This was probably a good move as when my alarm went off at 6.15pm I was in such a deep sleep that I was highly disoriented and confused as to why my alarm was going off at 6.15am.

We then got ready and headed down the subway to Grand station: we were heading to Howl at the Moon, a duelling piano bar to which we had free entry coupons from our Hop on Hop off tour. Sophie at been to one elsewhere in the US and loved it.

First, however, we needed dinner, and there was Rock Bottom Restaurant and Brewery just as we exited the station. Sophie had eaten this US chain before and recommended the food, so we went in.

This proved to be a very good choice. Our strawberry cocktails were delicious, and the ‘bourbonzola’ beef burger I had (bourbon sauce, gorgonzola and onion rings) was at least equal to the best burger I have ever had.

We headed to Howl at the Moon at about 9:30pm and proceeded to enjoy the amazing music of a four piece band that continually changed instruments, with everyone taking turns to sing and play two pianos, drums and a guitar. The audience requested songs and they played them straight away without music. They knew everything! After a short while I spied an empty table right at the front and Sophie and I had prime position for the rest of the night.

We requested ‘Highway to Hell’ by ACDC for something Australian, and then Sophie got ‘Chicken Fried’ for something country. Myself and a friendly New Yorker were ecstatic when Billy Joel’s ‘New York State of Mind’ came on (strangely requested by some people from Boston), and the two of us sang all the words up the front – although I feel we were two of the only people in the room who knew the song, let alone the words. They also played Frank Sinatra’s ‘Chicago’, which I requested.

You had to put money with your request, but Sophie and I were thrilled when the band played ‘Land Down Under’ for our benefit, although we didn’t request it! We stayed until close at 1:40am before heading across the road to another couple of bars with everyone else in the place who streamed across.

The next morning I had to check out so rose earlier than Sophie. I went to a nearby cafe that we had passed but not been into, but which two Irish men from our hostel, who we had met out after Howl at the Moon and shared a taxi with back to the hostel, had said we must go to. I ordered the turkey Panini and was not disappointed: it was extremely delicious. I savoured this gourmet fare while reading the Chicago Tribune.

I then walked to the foreshore, which Sophie had said I must check out. After sitting and admiring the view (you really wouldn’t know it wasn’t the ocean) I went downtown to walk around for a bit. I picked up the free popcorn that was associated with our Hop on Hop off tickets – a delicious mix of brown sugar and cheddar popcorn from a famous Chicago place that had evidently been the source of the delicious smell which had wafted to us on the bus tour. Although my free sample bag was not warm, I enjoyed it in front of the ‘bean’ in Millennium Park’.

I had meant to ride the Hop on Hop off bus again, but it took too long to come and I realised I would need to head back to the hostel to get my luggage and head to the bus stop. On the way back I stopped at ‘Chicago’s Dog House’, near the hostel, and had a delicious hotdog with Irish cheddar, caramelised onions and Dijon mustard. So ended the Chicago, and US trip. Til next time, USA!

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